It was found that alpha-aryl-alpha-diazocarboxylates react with variable regioselectivity in intramolecular rhodium-catalyzed C-H insertion reactions. 3-(Trialkoxysilyl)propyl esters underwent a clean cis-gamma-lactone formation (62-69%) if the aryl rest was a phenyl group while the analogous alpha-(2-bromophenyl)-alpha-diazocarboxylates produced the respective beta-lactones. In general beta-lactone formation was shown to be the only detectable C-H insertion pathway for the latter substrate class irrespective of the ester substituent. The beta-lactone products (eight examples) were obtained in yields of 41-68% with a diastereomeric ratio (dr) of 75:25 to 96:4 in favor of the trans diastereoisomer. The 2-bromo substituent could be displaced by an aryl group in a subsequent Suzuki cross-coupling reaction.
机构:Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China
Choi, MKW
Yu, WY
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Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R ChinaUniv Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China
Yu, WY
Che, CM
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机构:Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China
机构:Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China
Choi, MKW
Yu, WY
论文数: 0引用数: 0
h-index: 0
机构:
Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R ChinaUniv Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China
Yu, WY
Che, CM
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机构:Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China